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Title: Experimental Evidence of Dioxole Unimolecular Decay Pathway for Isoprene-Derived Criegee Intermediates

Abstract

Ozonolysis of isoprene, one of the most abundant volatile organic compounds emitted into the Earth’s atmosphere, generates two four-carbon unsaturated Criegee intermediates, methyl vinyl ketone oxide (MVK-oxide) and methacrolein oxide (MACR-oxide). The extended conjugation between the vinyl substituent and carbonyl oxide groups of these Criegee intermediates facilitates rapid electrocyclic ring closures that form 5-membered cyclic peroxides, known as dioxoles. This research discusses the first experimental evidence of this novel decay pathway, which is predicted to be the dominant atmospheric sink for specific conformational forms of MVK-oxide (anti) and MACR-oxide (syn) with the vinyl substituent adjacent to the terminal O atom. The resulting dioxoles are predicted to undergo rapid unimolecular decay to oxygenated hydrocarbon radical products, including acetyl, vinoxy, formyl, and 2-methyl-vinoxy radicals. In the presence of O2, these radicals rapidly react to form peroxy radicals (ROO), which quickly decay via carbon-centered radical intermediates (QOOH) to stable carbonyl products that are identified in this work. The carbonyl products are detected under thermal conditions (298 K, 10 torr He) using multiplexed photoionization mass spectrometry (MPIMS). The main products (and associated relative abundances) originating from unimolecular decay of anti-MVK-oxide and subsequent reaction with O2 are formaldehyde (88 ± 5%), ketene (9 ± 1%)more » and glyoxal (3 ± 1%). Those identified from the unimolecular decay of syn-MACR-oxide and subsequent reaction of O2 are acetaldehyde (37 ± 7%), vinyl alcohol (9 ± 1%), methylketene (2 ± 1%), and acrolein (52 ± 5%). In addition to the stable carbonyl products, the secondary peroxy chemistry also generates OH or HO2 radical co-products.« less

Authors:
 [1];  [2];  [3]; ORCiD logo [3];  [4];  [1]; ORCiD logo [1]; ORCiD logo [5];  [3]; ORCiD logo [6];  [6]; ORCiD logo [4]; ORCiD logo [1]
+ Show Author Affiliations
  1. Univ. of Pennsylvania, Philadelphia, PA (United States)
  2. California Institute of Technology (CalTech), Pasadena, CA (United States). Jet Propulsion Lab. (JPL); Sandia National Lab. (SNL-CA), Livermore, CA (United States); Argonne National Lab. (ANL), Argonne, IL (United States)
  3. California Institute of Technology (CalTech), Pasadena, CA (United States). Jet Propulsion Lab. (JPL)
  4. Sandia National Lab. (SNL-CA), Livermore, CA (United States)
  5. Sandia National Lab. (SNL-CA), Livermore, CA (United States
  6. Bristol Univ. (United Kingdom)
Publication Date:
Research Org.:
Univ. of Pennsylvania, Philadelphia, PA (United States); Argonne National Laboratory (ANL), Argonne, IL (United States); Sandia National Lab. (SNL-NM), Albuquerque, NM (United States); Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States); Sandia National Lab. (SNL-CA), Livermore, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences, and Biosciences Division; USDOE National Nuclear Security Administration (NNSA); National Aeronautics and Space Administration (NASA); National Science Foundation (NSF)
OSTI Identifier:
1633329
Alternate Identifier(s):
OSTI ID: 1644072; OSTI ID: 1660372; OSTI ID: 1782236
Report Number(s):
SAND-2020-7131J
Journal ID: ISSN 1089-5639
Grant/Contract Number:  
FG02-87ER13792; NA0003525; AC02-06CH11357; AC02-05CH11231; CHE-1902509; AC04-94AL85000
Resource Type:
Accepted Manuscript
Journal Name:
Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory
Additional Journal Information:
Journal Volume: 124; Journal Issue: 18; Journal ID: ISSN 1089-5639
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
09 BIOMASS FUELS; Chemical reactions; Photoionization; Energy; Aldehydes; Organic reactions

Citation Formats

Vansco, Michael F., Caravan, Rebecca L., Zuraski, Kristen, Winiberg, Frank A. F., Au, Kendrew, Trongsiriwat, Nisalak, Walsh, Patrick J., Osborn, David L., Percival, Carl J., Khan, M. Anwar H., Shallcross, Dudley E., Taatjes, Craig A., and Lester, Marsha I. Experimental Evidence of Dioxole Unimolecular Decay Pathway for Isoprene-Derived Criegee Intermediates. United States: N. p., 2020. Web. doi:10.1021/acs.jpca.0c02138.
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Vansco, Michael F., Caravan, Rebecca L., Zuraski, Kristen, Winiberg, Frank A. F., Au, Kendrew, Trongsiriwat, Nisalak, Walsh, Patrick J., Osborn, David L., Percival, Carl J., Khan, M. Anwar H., Shallcross, Dudley E., Taatjes, Craig A., & Lester, Marsha I. Experimental Evidence of Dioxole Unimolecular Decay Pathway for Isoprene-Derived Criegee Intermediates. United States. https://doi.org/10.1021/acs.jpca.0c02138
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Vansco, Michael F., Caravan, Rebecca L., Zuraski, Kristen, Winiberg, Frank A. F., Au, Kendrew, Trongsiriwat, Nisalak, Walsh, Patrick J., Osborn, David L., Percival, Carl J., Khan, M. Anwar H., Shallcross, Dudley E., Taatjes, Craig A., and Lester, Marsha I. Tue . "Experimental Evidence of Dioxole Unimolecular Decay Pathway for Isoprene-Derived Criegee Intermediates". United States. https://doi.org/10.1021/acs.jpca.0c02138. https://www.osti.gov/servlets/purl/1633329.
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@article{osti_1633329,
title = {Experimental Evidence of Dioxole Unimolecular Decay Pathway for Isoprene-Derived Criegee Intermediates},
author = {Vansco, Michael F. and Caravan, Rebecca L. and Zuraski, Kristen and Winiberg, Frank A. F. and Au, Kendrew and Trongsiriwat, Nisalak and Walsh, Patrick J. and Osborn, David L. and Percival, Carl J. and Khan, M. Anwar H. and Shallcross, Dudley E. and Taatjes, Craig A. and Lester, Marsha I.},
abstractNote = {Ozonolysis of isoprene, one of the most abundant volatile organic compounds emitted into the Earth’s atmosphere, generates two four-carbon unsaturated Criegee intermediates, methyl vinyl ketone oxide (MVK-oxide) and methacrolein oxide (MACR-oxide). The extended conjugation between the vinyl substituent and carbonyl oxide groups of these Criegee intermediates facilitates rapid electrocyclic ring closures that form 5-membered cyclic peroxides, known as dioxoles. This research discusses the first experimental evidence of this novel decay pathway, which is predicted to be the dominant atmospheric sink for specific conformational forms of MVK-oxide (anti) and MACR-oxide (syn) with the vinyl substituent adjacent to the terminal O atom. The resulting dioxoles are predicted to undergo rapid unimolecular decay to oxygenated hydrocarbon radical products, including acetyl, vinoxy, formyl, and 2-methyl-vinoxy radicals. In the presence of O2, these radicals rapidly react to form peroxy radicals (ROO), which quickly decay via carbon-centered radical intermediates (QOOH) to stable carbonyl products that are identified in this work. The carbonyl products are detected under thermal conditions (298 K, 10 torr He) using multiplexed photoionization mass spectrometry (MPIMS). The main products (and associated relative abundances) originating from unimolecular decay of anti-MVK-oxide and subsequent reaction with O2 are formaldehyde (88 ± 5%), ketene (9 ± 1%) and glyoxal (3 ± 1%). Those identified from the unimolecular decay of syn-MACR-oxide and subsequent reaction of O2 are acetaldehyde (37 ± 7%), vinyl alcohol (9 ± 1%), methylketene (2 ± 1%), and acrolein (52 ± 5%). In addition to the stable carbonyl products, the secondary peroxy chemistry also generates OH or HO2 radical co-products.},
doi = {10.1021/acs.jpca.0c02138},
journal = {Journal of Physical Chemistry. A, Molecules, Spectroscopy, Kinetics, Environment, and General Theory},
number = 18,
volume = 124,
place = {United States},
year = {Tue Apr 07 00:00:00 EDT 2020},
month = {Tue Apr 07 00:00:00 EDT 2020}
}
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https://doi.org/10.1021/acs.jpca.0c02138
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